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Chemical Compound Review

Arsenical     (2-aminophenyl)arsonic acid

Synonyms: CHEMBL346468, AG-K-74033, ACMC-209fae, ANW-24084, NSC-12611, ...
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Disease relevance of o-Arsanilic acid


Psychiatry related information on o-Arsanilic acid


High impact information on o-Arsanilic acid

  • In vitro, the MRPs can collectively confer resistance to natural product drugs and their conjugated metabolites, platinum compounds, folate antimetabolites, nucleoside and nucleotide analogs, arsenical and antimonial oxyanions, peptide-based agents, and, under certain circumstances, alkylating agents [7].
  • Arsenical-resistant trypanosomes lack an unusual adenosine transporter [2].
  • A significant 19th century public health problem was that the inhabitants of many houses containing wallpaper decorated with green arsenical pigments experienced illness and death [8].
  • The patient had taken an arsenical preparation during a period of 12 yr because of psoriasis and subsequently developed keratotic changes of the palms and soles of his feet and an epithelioma of the scrotum [4].
  • To examine the role of PML in mediating arsenical activity, we also tested these agents using murine embryonic fibroblasts (MEFs) and bone marrow (BM) progenitors in which the PML gene had been inactivated by homologous recombination [9].

Chemical compound and disease context of o-Arsanilic acid


Biological context of o-Arsanilic acid


Anatomical context of o-Arsanilic acid


Associations of o-Arsanilic acid with other chemical compounds

  • The synthetic tripeptide arsenical 4-(N-(S-glutathionylacetyl)amino)p-phenylarsenoxide (p-GSAO) is an angiogenesis inhibitor that inactivates mitochondrial adenine nucleotide translocase (ANT) by cross-linking a pair of matrix-facing cysteine residues [24].
  • In our studies of the effects of the trivalent arsenical phenylarsine oxide on insulin-dependent hexose uptake in 3T3-L1 adipocytes, we needed direct methods to study arsenical-protein interactions [25].
  • Phospho-422(aP2) protein (pp15) accumulates in cells treated with insulin and PAO because the arsenical blocks turnover of the phosphoryl group of pp15 [26].
  • It seems therefore that selection for resistance to either pentamidine or arsenical drugs can result in a similar phenotype of reduced drug accumulation, explaining the occurrence of cross-resistance [27].
  • We also show that a laboratory line of Trypanosoma brucei gambiense, adapted to high levels of resistance for the melaminophenyl arsenical drug melarsamine hydrochloride (Cymelarsan), had similarly lost TbAT1 and HAPT1 activity while retaining LAPT1 activity [27].

Gene context of o-Arsanilic acid


Analytical, diagnostic and therapeutic context of o-Arsanilic acid


  1. Vinyl-chloride-induced liver disease. From idiopathic portal hypertension (Banti's syndrome) to Angiosarcomas. Thomas, L.B., Popper, H., Berk, P.D., Selikoff, I., Falk, H. N. Engl. J. Med. (1975) [Pubmed]
  2. Arsenical-resistant trypanosomes lack an unusual adenosine transporter. Carter, N.S., Fairlamb, A.H. Nature (1993) [Pubmed]
  3. Disulfide exchange in domain 2 of CD4 is required for entry of HIV-1. Matthias, L.J., Yam, P.T., Jiang, X.M., Vandegraaff, N., Li, P., Poumbourios, P., Donoghue, N., Hogg, P.J. Nat. Immunol. (2002) [Pubmed]
  4. Noncirrhotic presinusoidal portal hypertension associated with chronic arsenical intoxication. Huet, P.M., Guillaume, E., Cote, J., Légaré, A., Lavoie, P., Viallet, A. Gastroenterology (1975) [Pubmed]
  5. Arsenical air pollution and lung cancer. Stellman, J.M., Kabat, G.C. Lancet (1978) [Pubmed]
  6. Cutaneous manifestations of chronic arsenicism: review of seventeen cases. Wong, S.S., Tan, K.C., Goh, C.L. J. Am. Acad. Dermatol. (1998) [Pubmed]
  7. Transmembrane transport of endo- and xenobiotics by mammalian ATP-binding cassette multidrug resistance proteins. Deeley, R.G., Westlake, C., Cole, S.P. Physiol. Rev. (2006) [Pubmed]
  8. Microbial methylation of metalloids: arsenic, antimony, and bismuth. Bentley, R., Chasteen, T.G. Microbiol. Mol. Biol. Rev. (2002) [Pubmed]
  9. Arsenic trioxide and melarsoprol induce programmed cell death in myeloid leukemia cell lines and function in a PML and PML-RARalpha independent manner. Wang, Z.G., Rivi, R., Delva, L., König, A., Scheinberg, D.A., Gambacorti-Passerini, C., Gabrilove, J.L., Warrell, R.P., Pandolfi, P.P. Blood (1998) [Pubmed]
  10. Idiopathic portal hypertension. Villeneuve, J.P., Huet, P.M., Joly, J.G., Marleau, D., Côté, J., Légaré, A., Lafortune, M., Lavoie, P., Viallet, A. Am. J. Med. (1976) [Pubmed]
  11. Identification of an essential cysteinyl residue in the ArsC arsenate reductase of plasmid R773. Liu, J., Gladysheva, T.B., Lee, L., Rosen, B.P. Biochemistry (1995) [Pubmed]
  12. Combination chemotherapy of drug-resistant Trypanosoma brucei rhodesiense infections in mice using DL-alpha-difluoromethylornithine and standard trypanocides. Bacchi, C.J., Nathan, H.C., Yarlett, N., Goldberg, B., McCann, P.P., Sjoerdsma, A., Saric, M., Clarkson, A.B. Antimicrob. Agents Chemother. (1994) [Pubmed]
  13. Targeting of Toxic Compounds to the Trypanosome's Interior. Barrett, M.P., Gilbert, I.H. Adv. Parasitol. (2006) [Pubmed]
  14. The epidemiology of soft tissue sarcoma. Zahm, S.H., Fraumeni, J.F. Semin. Oncol. (1997) [Pubmed]
  15. Comparative activity of melarsoprol and arsenic trioxide in chronic B-cell leukemia lines. König, A., Wrazel, L., Warrell, R.P., Rivi, R., Pandolfi, P.P., Jakubowski, A., Gabrilove, J.L. Blood (1997) [Pubmed]
  16. Pharmacological characterization of multidrug resistant MRP-transfected human tumor cells. Cole, S.P., Sparks, K.E., Fraser, K., Loe, D.W., Grant, C.E., Wilson, G.M., Deeley, R.G. Cancer Res. (1994) [Pubmed]
  17. Molecular characterization of an anion pump. The arsA gene product is an arsenite(antimonate)-stimulated ATPase. Rosen, B.P., Weigel, U., Karkaria, C., Gangola, P. J. Biol. Chem. (1988) [Pubmed]
  18. Interaction of ATP binding sites in the ArsA ATPase, the catalytic subunit of the Ars pump. Li, J., Liu, S., Rosen, B.P. J. Biol. Chem. (1996) [Pubmed]
  19. Nucleotide sequence of the structural genes for an anion pump. The plasmid-encoded arsenical resistance operon. Chen, C.M., Misra, T.K., Silver, S., Rosen, B.P. J. Biol. Chem. (1986) [Pubmed]
  20. Arsenic trioxide and melarsoprol induce apoptosis in plasma cell lines and in plasma cells from myeloma patients. Rousselot, P., Labaume, S., Marolleau, J.P., Larghero, J., Noguera, M.H., Brouet, J.C., Fermand, J.P. Cancer Res. (1999) [Pubmed]
  21. Complete and reversible inhibition of NADPH oxidase in human neutrophils by phenylarsine oxide at a step distal to membrane translocation of the enzyme subunits. Le Cabec, V., Maridonneau-Parini, I. J. Biol. Chem. (1995) [Pubmed]
  22. Sulfhydryl regulation of L-selectin shedding: phenylarsine oxide promotes activation-independent L-selectin shedding from leukocytes. Bennett, T.A., Edwards, B.S., Sklar, L.A., Rogelj, S. J. Immunol. (2000) [Pubmed]
  23. Inhibition of coupling factor B activity by cadmium ion, arsenite-2,3-dimercaptopropanol, and phenylarsine oxide, and preferential reactivation by dithiols. Joshi, S., Hughes, J.B. J. Biol. Chem. (1981) [Pubmed]
  24. Para to ortho repositioning of the arsenical moiety of the angiogenesis inhibitor 4-(N-(S-glutathionylacetyl)amino)phenylarsenoxide results in a markedly increased cellular accumulation and antiproliferative activity. Dilda, P.J., Decollogne, S., Rossiter-Thornton, M., Hogg, P.J. Cancer Res. (2005) [Pubmed]
  25. Iodophenylarsine oxide and arsenical affinity chromatography: new probes for dithiol proteins. Application to tubulins and to components of the insulin receptor-glucose transporter signal transduction pathway. Hoffman, R.D., Lane, M.D. J. Biol. Chem. (1992) [Pubmed]
  26. Phosphotyrosyl turnover in insulin signaling. Characterization of two membrane-bound pp15 protein tyrosine phosphatases from 3T3-L1 adipocytes. Liao, K., Hoffman, R.D., Lane, M.D. J. Biol. Chem. (1991) [Pubmed]
  27. Loss of the High-Affinity Pentamidine Transporter Is Responsible for High Levels of Cross-Resistance between Arsenical and Diamidine Drugs in African Trypanosomes. Bridges, D.J., Gould, M.K., Nerima, B., Mäser, P., Burchmore, R.J., de Koning, H.P. Mol. Pharmacol. (2007) [Pubmed]
  28. Purification and characterization of ACR2p, the Saccharomyces cerevisiae arsenate reductase. Mukhopadhyay, R., Shi, J., Rosen, B.P. J. Biol. Chem. (2000) [Pubmed]
  29. Diarsenic and tetraarsenic oxide inhibit cell cycle progression and bFGF- and VEGF-induced proliferation of human endothelial cells. Woo, S.H., Park, M.J., An, S., Lee, H.C., Jin, H.O., Lee, S.J., Gwak, H.S., Park, I.C., Hong, S.I., Rhee, C.H. J. Cell. Biochem. (2005) [Pubmed]
  30. Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms. Sakurai, T., Kaise, T., Matsubara, C. Chem. Res. Toxicol. (1998) [Pubmed]
  31. Isolation of three contiguous genes, ACR1, ACR2 and ACR3, involved in resistance to arsenic compounds in the yeast Saccharomyces cerevisiae. Bobrowicz, P., Wysocki, R., Owsianik, G., Goffeau, A., Ułaszewski, S. Yeast (1997) [Pubmed]
  32. Overexpression of the putative thiol conjugate transporter TbMRPA causes melarsoprol resistance in Trypanosoma brucei. Shahi, S.K., Krauth-Siegel, R.L., Clayton, C.E. Mol. Microbiol. (2002) [Pubmed]
  33. Crystallization and preliminary X-ray diffraction analysis of the ArsC protein from the Escherichia coli arsenical resistance plasmid, R773. de Mel, V.S., Doyle, M.A., Gladysheva, T.B., Oden, K.L., Martin, P.D., Rosen, B.P., Edwards, B.F. J. Mol. Biol. (1994) [Pubmed]
  34. Arsenic induces human keratinocyte apoptosis by the FAS/FAS ligand pathway, which correlates with alterations in nuclear factor-kappa B and activator protein-1 activity. Liao, W.T., Chang, K.L., Yu, C.L., Chen, G.S., Chang, L.W., Yu, H.S. J. Invest. Dermatol. (2004) [Pubmed]
  35. Vitamin D analogs in cutaneous malignancies. Majewski, S., Kutner, A., Jabłonska, S. Curr. Pharm. Des. (2000) [Pubmed]
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